My Tall Mistresses Pt. 03

I try to escape with all the energy I have but Michelle holds me too firmly. I cover my butthole with my hands and I yell that I will not give up on this. Sandra, as always, knows what to say,

"If you don't calm down right now, I will fuck you without any lube. It's going to hurt a lot. So you better decide wisely. Lube or not lube?"

"I never agreed to this," I complain.

"You agreed to have sex with me," points out Sandra, "What are we supposed to do? Do you think you can penetrate me with that tiny shrimp? I don't think so. So if you can't penetrate me, I will penetrate you. I know this is an important moment for you: I am about to take your virginity, and I understand if you are stressed about it. But it's better that you calm down and accept the reality of the situation. I will ask you again: lube or not lube? Choose wisely."

"Lube," I reply with a low tone of voice, dying of humiliation.

She applies a lot of lube. As soon as she touches my butthole, involuntarily, I start moaning.

"He already likes it!" says Michelle. I see her face looking at me from above as she is holding me down from the heels. She is smiling.

"Oh, if he likes it now, I can only imagine how much he's going to like it in a few minutes," adds Sandra.

I feel the tip of her strapon on my hole. "Just the tip?" she asks, but then says "Just joking," and pushes her strapon deep in.

After a few seconds, she penetrates me completely. I don't feel pain, but a wave of uncontrollable pleasure, and Sandra has full control over it.

I hear Michelle saying with a tone of surprise "Oh, he's moaning like a girl..."

Sandra pulls me far from Michelle and fucks me from above. With her hands, she pushes the back of my knees down to the sides of my head. "You must look at me in the eyes when I fuck you," she says, "I enjoy seeing the pleasure in your face and the humiliation in your eyes."

At some point, she puts her arms around my back and lifts me so that I sit on her while she sits on the bed. Even if I am sitting on her pelvis, she still towers over me, and this makes me feel even smaller than I am. Then, Sandra looks at me and says, "Are you ready?"

I don't have time to reply that she stands up. She fucks me while standing and holding my ass with her hands. It seems effortless for her. She turns around while fucking me, and I see Michelle on the bed with one hand on her vagina: she is masturbating looking at us. Every few seconds, she cheers Sandra saying, "Oh Sandra, you are so good. You are fucking him and he's screaming like a girl."

Sandra doesn't pay much attention to what Michelle is saying. Her eyes are all on me, making sure she can capture every expression my face makes. Then, she put me against the wall, leaned her pelvis so that she could hold me up without using her hands, grabbed both my wrists, and spread my arms to the wall. I am impaled to the wall by a 23-year-old girl. My legs are floating in midair while hers are strong supporting all my weight. She exclaims, "It sounds like you are enjoying a lot!"

My ego makes me reply promptly, "No! That's not true!"

"Oh Timmy... One more time you are not being honest with us and with yourself. We can see and we can hear that you are having the best time of your life! Luckily, I feel like helping you clear your mind from all this confusion." says Sandra with her typical wicked tone. I sense some more humiliation coming.

She looks at Michelle and says, "Michelle, please, put a 30-second timer with your phone. That's all I need." Then she looks back at me and continues, "I will fuck you hard now. You are going to feel a much stronger pleasure than before. If it's true that you are not enjoying all this, all you have to do is to just not come. On the other hand, if you feel like admitting that you enjoy being lift-fucked with a strapon by a much younger girl who locked your tiny dick in a chastity cage, all you have to do is to come within the next 30 seconds."

'What does she mean? How can I possibly come if my dick is locked up?' I ask myself.

Sandra holds me again with her hands on my ass and starts lift-fucking me with a much faster rhythm than before. I hear Michelle screaming, "Faster... Harder..."

After only 5 seconds, I feel a wave of pleasure that runs all over my body. All of a sudden, a liquid comes off from my locked penis. Was this an orgasm? It was somehow different from the typical orgasms I had experienced so far masturbating myself. It was much stronger. I couldn't believe it: she made me come by fucking me from the ass, with my dick in a chastity device, and without even touching it.

"There it is! You came much faster than I thought! I was being very pessimistic giving you 30 seconds, you only needed 5." says Sandra before exploding in a laugh.

"What? That's not true... I did not come," I negate the evidence.

Sandra sits on the bed, I am still impaled to her strapon. Michelle comes closer, with her finger she takes some of my excretion and puts it to my lips. "Maybe you want to taste it to believe it?" I am paralyzed.

"Little Timmy. This was an assgasm: an orgasm from the ass. You reach an assgasm when two conditions are satisfied: first, you must really like enjoy being penetrated in the ass, second, the one fucking you must be exceptionally hot." says Sandra with her typical teaching tone.

Michelle sits on the side of Sandra and asks, "Be honest now Timmy. You just came. Did you feel pleasure?"

"I did feel pleasure," I reply.

"Did you like coming while being fucked like a girl?", Michelle keeps asking.

"Yes..." I reply humiliated.

"And so, what do we say in this case to the person, Sandra, that made you discover your true nature and, at the same time, made you feel so good?"

"Thank you, Sandra," I reply. Sandra grabs my ball and corrects me, "Thank you, MISTRESS."

"Thank you, Mistress," I say promptly.

"Great! You are a fast learner afterall," concludes Sandra.